Prior to Red Hat, Young built a couple of computer rental and leasing businesses, including founding Vernon Computer Rentals in 1984.[2] Descendants of Vernon are still operating under that name. After leaving Vernon, Young founded the ACC Corp Inc. in 1993.

Marc Ewing and Young's partnership started in 1994 when ACC acquired the Red Hat trademarks from Ewing. In early 1995, ACC changed its name to Red Hat Software, which has subsequently changed to simply Red Hat, Inc. Young served as Red Hat's CEO until 1999.

After leaving Red Hat he founded Lulu.com in 2002, a self-publishing web-site that claims to be the world's fastest-growing provider of print-on-demand books. He is Lulu's CEO. In 2006 Young established the Lulu Blooker Prize, a book prize for books that began as blogs. He launched the prize partly as a means of promoting Lulu.

Today the Internet connects every single one of your customers, not just to you but to each other. So you produce a lemon of a car and you won’t know where to hide because your customers are going to tell each other about it and then the rest of the world about it. So it is actually a fundamentally healthy thing from a consumer point of view.

Conversely if you do have a better product suddenly you have these businesses that grow like topsy. If you come up with an innovation that serves, that resonates with customers, the Internet will allow that innovation to spread dramatically faster than any other technology has enabled a new innovation to be adopted in the history of mankind.[3]

Joyce Young, Bob Young's aunt, purchased stock in Red Hat Inc. shortly after its founding. When Red Hat's stock rose significantly after its initial public offering in 1999, she and her husband sold enough stock to recoup their initial investment, and retained some stocks. By January 2000, the remaining stock was valued in the millions. In June 2000, she donated $40 million to the Hamilton Community Foundation to be used largely in improvement of Hamilton-area health facilities, an act that represented one of the single largest charitable donations in Canadian history. The couple also made significant donations to the Royal Military College of Canada.